1-Decanol → Decyl methanesulfonate

HRID 259065Notes

Reaction equation

HRID 259065 reaction equation
[CH2:1]([OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[S:12](Cl)([CH3:15])(=[O:14])=[O:13]>N1C(C)=CC(C)=CC=1C.CCCCCC>[CH3:15][S:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 81741-DecanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 5235508Decyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 79532,4,6-TrimethylpyridineSolventHCID 8058HexaneSolvent

Procedure

To a cooled solution of 158.3 grams of 1-decanol in 1.0 liter of collidine is added dropwise 126 grams of mesyl chloride. The resulting mixture is stirred at room temperature for 1.5 hours and then poured onto ice. The reaction mixture is extracted with ether and the ether extracts are washed with 10% hydrochloric acid. The ether extracts are combined, dried over anhydrous sodium sulfate, and the solvent removed under reduced pressure to leave an oil which solidifies upon cooling. The oil is dissolved in n-hexane and cooled to yield as crystals, decyl methylsulfonate.

Workup

  1. additionpoured onto ice
  2. extractionThe reaction mixture is extracted with ether
  3. washthe ether extracts are washed with 10% hydrochloric acid
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customto leave an oil which
  7. temperatureupon cooling
  8. temperaturecooled

Sources & evidence

ORD record
ord-ecfa66b8ed5a4dfd8452d31c022d96ea
Source dataset
uspto-grants-1977_07
Patent number
US04036828

Reaction notes

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